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$6,300,000
3 Beds ⋅ 2 Baths ⋅ 202605681 MLS ⋅ FS - Fee Simple Tenure
A rare opportunity to acquire an incredible Honolulu estate. Built in 1908 by Alfred Castle, this remarkable 13+ acre Tantalus property has been held by just four distinguished families, Castle, McCandless-Marks, Dillingham lineages, and the estate of Juan Hamilton—renowned artist and protégé of Georgia O’Keeffe. A stately drive welcomes you with eucalyptus trees where expansive lawns evoke the elegance of a bygone era and invite grand outdoor gatherings. Panoramic views from Diamond Head to Haleiwa showcase striking sunsets over the Pacific. Fragrant puakenikeni, jasmine and white ginger bloom amid a landscape of moss rock walls, brick pathways, and wooded trails. The buildings are rich with historic details and distinctive architectural finishes. A 60,000-gallon water catchment system underscores the estate’s blend of heritage and stewardship. More than a residence, this is a landmark property awaiting its next chapter—a chance to reimagine one of Honolulu’s great estates. For those drawn to the intersection of history, nature and place, this extraordinary offering represents far more than real estate. It is a legacy to inherit, shape, and preserve for generations to come.

3330 Tantalus Drive, Honolulu

Listing courtesy of Compass.

$1,680,000
3 Beds ⋅ 3 Baths ⋅ 202601029 MLS ⋅ FS - Fee Simple Tenure
Nestled in lush Tantalus, above the Honolulu cityscape, this 3BD/3BA retreat offers privacy, nature, & modern comfort on a 0.40-acre lot surrounded by tropical greenery. Built in 1975 & updated in 1987, the home features soaring ceilings, rich redwood walls, & warm wood tones throughout. Its flexible layout includes an open kitchen & 3 living rooms, one on each level, making this property ideal for single family or multi-family living. Sunlight pours through large windows, showcasing stunning views, while 31 PV panels with battery backup provide energy efficiency. Sip your morning coffee on one of three wrap-around covered lanais, enjoy your fenced garden patio, or play on your flat, terraced yard space—rare for the area—supported by beautiful, newly-engineered rock retaining walls. The detached 2-car garage adds convenience, & the forested setting enhances the serene ambiance of this home. Explore the terrain on your own lot or venture out. You're minutes from Pu'u 'Ualaka'a State Park & hiking trails, yet still close to downtown and schools. This home perfectly balances seclusion & accessibility. A true sanctuary to embrace Hawaii’s beauty & island living!

4142 Round Top Drive, Honolulu

Listing courtesy of Compass.

$1,695,000
4 Beds ⋅ 3 Baths ⋅ 202605317 MLS ⋅ FS - Fee Simple Tenure
NEW PRICE! Tucked away in a private, forested mountainside enclave, this rare architectural estate by noted architect Charles Chamberland offers a striking blend of mid-century modern heritage and smart, flexible living. Enveloped by trees and a stunningly peaceful setting this 4-bedroom, 3-bath gem provides nearly 3,000 sq. ft. of living space masterfully designed to accommodate multi-generational families with separate private entrances. Refreshed with new paint and carpet, the upper levels feature an expansive open floor plan anchored by soaring ceilings and floor-to-ceiling windows that perfectly frame the lush, verdant surroundings. The gourmet kitchen combines timeless mahogany cabinetry with elegant marble floors, leading up to a loft-style primary suite. The first-level layout provides the perfect separation of space, allowing for potential rental, secured with hurricane shutters. The estate features world-class botanical grounds that flow seamlessly into the forest, offering peaceful sitting areas, winding trails, and tranquil water features. Unwind on the scenic third-level landing with peek-a-boo ocean views. Your ultimate, flexible nature retreat awaits. Sold as is.

156 Forest Ridge Way, Honolulu

Listing courtesy of REMAX Hawaii.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.